108534-47-0

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is used as a protecting group in the synthesis of pharmaceuticals for the development of new drugs. The tert-butyldimethylsilyloxy group shields the phenolic hydroxyl group, allowing for selective reactions to occur at other functional groups, which is crucial for the synthesis of complex drug molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is employed as a protecting group in the synthesis of agrochemicals, such as pesticides and herbicides. The protection of phenolic hydroxyl groups enables selective reactions, facilitating the development of effective and targeted agrochemicals.
Used in Natural Product Synthesis:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is used as a protecting group in the synthesis of natural products, including the development of bioactive compounds derived from plants, fungi, and other natural sources. The selective protection of phenolic hydroxyl groups allows for the synthesis of complex natural product structures with potential therapeutic applications.
Used in Organic Synthesis Research:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is utilized as a protecting group in organic synthesis research to explore new reaction pathways and develop innovative synthetic methods. The selective protection of phenolic hydroxyl groups enables chemists to investigate reactions at other functional groups, leading to the discovery of new synthetic strategies and applications.

InChI:InChI=1/C12H20O2Si/c1-12(2,3)15(4,5)14-11-8-6-10(13)7-9-11/h6-9,13H,1-5H3

Upstream product

• 120743-89-7 4-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-cyclohexa-2,5-dienol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 123-31-9 hydroquinone 
• 123844-15-5 [4-(Adamantan-2-ylidene-phenyl-methoxy)-phenoxy]-tert-butyl-dimethyl-silane 
• 103-16-2 4-Benzyloxyphenol 
• 78018-57-2 1,4-bis{[(tert-butyl)(dimethyl)silyl]oxy}benzene 
• 299917-31-0 [4-(Tetrahydropyran-2-yloxy)phenoxy]-tert-butyldimethylsilane 
• 288-32-4 1H-imidazole 
• 108534-51-6 4-((tert-butyldimethylsilyl)oxy)-4-methoxycyclohexa-2,5-dienone 
• 74293-60-0 (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 108-24-7 acetic anhydride 
• 313547-95-4 (3R,4R,5R)-3-[(tert-butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone 

Downstream Products

• 108534-51-6 4-((tert-butyldimethylsilyl)oxy)-4-methoxycyclohexa-2,5-dienone 
• 188047-98-5 2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-phenylsulfanyl]-isoindole-1,3-dione 
• 159182-09-9 3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide 
• 299917-31-0 [4-(Tetrahydropyran-2-yloxy)phenoxy]-tert-butyldimethylsilane 
• 299917-32-1 2-Bromo-4-(tert-butyldimethylsilyloxy)phenol 
• 319426-10-3 tert-butyl-[4-(3,4-dihydro-2H-pyran-2-ylmethoxy)-phenoxy]-dimethyl-silane 
• 817602-44-1 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride 
• 1029559-01-0 2-{[4-(tert-butyldimethylsiloxy)phenoxy]methyl}oxirane 
• 1072798-29-8 tert-butyl 4-(tert-butyldimethylsilyloxy)phenyl carbonate 
• 1608486-19-6 C₃₆H₄₇NO₄Si 
• 1608486-17-4 C₇₇H₉₂O₁₃Si 
• 1608486-18-5 C₇₁H₇₈O₁₃ 
• 497-76-7 4-hydroxyphenyl α-D-glucopyranoside 

Relevant academic research and scientific papers

Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material fo

A new dendrimer series: synthesis, free radical scavenging and protein binding studies

Tri-o-tolyl benzene-1,3,5-tricarboxylate (TOBT (T0)), tri-4-hydroxyphenyl benzene-1,3,5-tricarboxylate (THBT (T1)), and tri-3,5-dihydroxyphenyl benzene-1,3,5-tricarboxylate (TDBT (T2)), a series of 1sttier dendrimers with a common 1,3,5-benzenetricarbonyl trichloride/trimesoyl chloride (TMC) core, are reported.T0does not have any replaceable H+on its terminal phenyl group, acting as a branch.T1has one phenolic -OH at theparaposition andT2has two phenolic -OH groups at the 3 and 5 positions of each terminal phenyl group. During synthesis, these -OH groups at the terminal phenyl groups were protected throughtert-butyldimethylsilyl chloride (TBDMSCl) assisted witht-BuOK in DCM, THF, indazole, 4-dimethylaminopyridine (DMAP), and tertiary-n-butyl ammonium fluoride (TBAF). MTBDMSP (mono-tertiary butyl dimethylsilane phloroglucinol), DTBDMSP (di-tertiary butyl dimethylsilane phloroglucinol), and TTBDMSP (tri-tertiary butyl dimethylsilane phloroglucinol) were obtained with >90percent yield, and TTBDMSP phenolic derivatives (PDs) were developed to synthesizeT0,T1, andT2dendrimers by deprotecting with TBAF.T0showed superhydrophobic properties as it did not dissolve in methanol, contrary toT1andT2, but dissolved in acetone. Their structures were determined using1H and13C NMR spectroscopies, and mass spectrometry. Their scavenging activities were studied using UV-Vis spectrophotometry compared with ascorbic acid and protein binding was studied with bovine serum albumin (BSA) and lysozyme (lyso).T0exhibited exceptional optical activity contrary toT1andT2, which acted as antioxidants to scavenge free radicals.

Efficient preparation of apically substituted diamondoid derivatives

We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as t

Total Synthesis and Structure Revision of Halioxepine

The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

Structure-aided optimization of non-nucleoside M. tuberculosis thymidylate kinase inhibitors

Mycobacterium tuberculosis thymidylate kinase (MtTMPK) has emerged as an attractive target for rational drug design. We recently investigated new families of non-nucleoside MtTMPK inhibitors in an effort to diversify MtTMPK inhibitor chemical space. We here report a new series of MtTMPK inhibitors by combining the Topliss scheme with rational drug design approaches, fueled by two co-crystal structures of MtTMPK in complex with developed inhibitors. These efforts furnished the most potent MtTMPK inhibitors in our assay, with two analogues displaying low micromolar MIC values against H37Rv Mtb. Prepared inhibitors address new sub-sites in the MtTMPK nucleotide binding pocket, thereby offering new insights into its druggability. We studied the role of efflux pumps as well as the impact of cell wall permeabilizers for selected compounds to potentially provide an explanation for the lack of correlation between potent enzyme inhibition and whole-cell activity.

Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Selective ether bond breaking method of aryl alkyl ether

The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.

Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale

A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.

METHOD TO GENERATE MICROCAPSULES WITH HEXAHYDROTRIAZINE (HT)-CONTAINING SHELLS

Materials and methods for preparing a payload-containing microcapsule with walls that have hexahydrotriazine (HT) and/or hemiaminal (HA) structures are disclosed. To an HT small molecule or a HA small molecule, or a combination thereof, in a solvent is ad